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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 630407Generated: October 30, 2026

Triethylamine → 4-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamide

https://huagongshe.com/reaction/630407

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantEthyl AcetateHCID 8857—
Reactant4-Bromobutyryl chlorideHCID 70225—
Reactant4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyanilineHCID 67145657—
SolventTetrahydrofuranHCID 8028—
Product4-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamideHCID 86677217—

Reaction Steps

To a solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline (intermediate 39; 0.75 g, 2.48 mmol) in tetrahydrofuran (20 mL) and triethylamine (0.38 mL, 2.73 mmol) was added under nitrogen atmosphere at 0° C. 4-bromobutanoyl chloride (0.32 mL, 2.76 mmol). The mixture was stirred for half an hour. Ethyl acetate was added to the mixture and the organic layer was washed with bicarbonate and brine, dried and the solvent was removed under reduced pressure. The title compound was obtained (97%) and it was used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315463B2
Source datasetuspto-grants-2016_04
ORD IDord-191337b7391a43d0825edefa616fc92a
Source noteuspto-grants-2016_04